Catalytic Asymmetric Synthesis of the Pentacyclic Core of (+)-Citrinadin A

Org Lett. 2021 Jul 2;23(13):4981-4985. doi: 10.1021/acs.orglett.1c01389. Epub 2021 Jun 11.

Abstract

The synthesis of the pentacylic core of (+)-citrinadin A is described. Our strategy harnesses the power of palladium-catalyzed trimethylenemethane chemistry (Pd-TMM) to form the key spirooxindole motif in a catalytic, asymmetric fashion. Upon the conversion of this spirooxindole to a vinyl epoxide electrophile, the piperidine ring is directly added via a diastereoselective metalation followed by an SN2' addition. The final ring of the pentacyclic core is then formed through an intramolecular SN2 displacement of the resulting activated alcohol.

Publication types

  • Research Support, Non-U.S. Gov't